2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89739681, Verbindung

HRID 1521800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521800
[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH:9]=[CH:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 123269771,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)

Produkt 1

HCID 89739681HCID 89739681, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a stirred solution of 1,1′-(4,5-dihydronaphtho[1,2-b]thiophene-2,7-diyl))diethanone (5c) (1 g, 3.7 mmol) in 30 ml of toluene, DDQ (0.84 g, 3.7 mmol) was added and the mixture was stirred at 110° C. for 60 hr. The reaction mixture was concentrated under reduced pressure, 100 ml water was added and the organics were extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography to obtain 1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)diethanone as a brown solid (10a) (0.45 g, 55%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 100 ml water
  2. additionwas added
  3. extractionthe organics were extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude compound which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e6f76e7971904a48b97accfc62652a67
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073942B2

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